DO ALL MEN MAKE GOOD SISSYMAIDS?
from Judy

Dear Helga,

I took Lucy shopping later in the afternoon after she finished the laundry. Most of the shopping was for me while Lucy tagged along to get educated on women's clothing. Normally before there was a Lucy all the shopping was done by me. Paul would rather stay home than go shopping. Now Lucy will go shopping when I want her too even if it isn't for her. We did end up looking at dildos and strapons as the last stop before going home. The store had more of a selection when it came to dildos than it did strapons. The good thing is the 3 strapons they had in stock were of higher quality. I looked at some online that had very flimsy looking straps that didn't look like they would hold up. When we saw the ones at the store today even Lucy commented on how well made they appeared. Lucy picked the size she thought would work best for her however I picked the next size larger with the argument that she would get used to it. After going back and forth I won so we bought the bigger one. It isn't that big Helga, just a bit thicker.

We picked up dinner on the way home instead of cooking every day. I asked Lucy if she wouldn't mind changing before we had dinner. That was just to get her in the habit of wearing her uniform at home. There was no argument so she did what I asked then served us dinner. Always keeping in mind that Lucy could sometimes feel inadequate as a man, I'm always careful not to do anything that could change her mood. In order to try out my new strapon later asking Lucy to do things rather than give her orders got better results. Hours later it was time for me to have my bath and Lucy to help me.

After my bath Lucy went to get changed into her nightie but this time I asked her to keep her bra on for a change. I like the look of her when she wears a bra with her big fake boobs. Without question Lucy did as I asked. She went to turn off all the lights and set the alarm giving me time to get the strapon ready. When Lucy returned she saw my strapon sticking out of my nightie. Usually Lucy lays on her back when getting the dildo treatment but tonight I wanted to give it to her doggie style.

Lucy leaned over the bed pulling her nightie up for me as I took her panties off. I asked Lucy if she was nervous snapping a rubber glove for her to hear. She joked asking me to be nice and that she did a good job today. That made me laugh as she was trying to bargain with me. After getting the strapon all lubed up with some on her bum as well I started sliding the strapon in inch by inch. Lucy adjusted her position while I held her waist ensuring the strapon stayed in place. I talked to Lucy while giving her my strapon telling her how nice it felt for me and how much I loved the fact she was into it too.

With having used my dildo on her many times I knew how much she could take before fighting back. I continued to fuck her slow and steady ensuring the strapon went in far enough each time. Lucy was bucking some but nothing too serious so I kept it up hearing her moaning. I asked her if she was doing alright which she was thank god. Stopping wasn't the answer I wanted to hear while just getting into it myself. I decided to go deeper but thought to ask Lucy first so no surprises keeping in mind how sensitive she can be.

Lucy agreed I could try going deeper which I did a bit at a time until minutes later she was taking the whole thing. Oh sure she was moaning while I held her tight picking up momentum. Before long I was fucking Lucy like she would have done to me if she had a penis. Every other stroke she tried to say something but couldn't spit it out so I kept going. A few minutes later I slowed to a stop panting like a dog. I told Lucy she was amazing, surprising the hell out of me. Washing her down then changing positions so she could give me oral seemed appropriate to me.

Lucy asked if she could go to sleep probably to rest her bum after a workout. I on the other hand wasn't tired so instead I sit here writing an a few e-mails. Helga I am quite pleased with the way Lucy is working out after not knowing how she might react to being my maid. There is no reason at all now that Lucy can't be my sissymaid other than her getting past the word. She does challenge me wanting to know why quite often until I give her an answer that satisfies her for the time being.

Lucy has lots to learn before she would be classified as a good sissymaid. What I like about Lucy is she always tries to do something instead of complaining about it. She has learned to dress herself, apply makeup, tweeze her eyebrows and keeps her body hair free. As far as her tasks go cleaning is good, laundry is good, ironing is good, cooking is coming along and attending to me is very good.

The more she gets involved with being my maid, soon to be sissymaid, the more I love her for it. Most people wouldn't believe me when I say that introducing Lucy to this life has improved our relationship more than you can imagine. Paul was always a very special guy but Lucy is even more special again. She is so respectful of me now that I have to pinch myself to see if this is a dream sometimes. It's the simple things like asking me if I would like a tea, coffee, something to snack on or a back rub. These are things that Lucy makes time to ask me in between doing laundry, cleaning toilets or ironing.

It surprises me every day that she thinks of me while performing jobs I gave to her to do. Helga do you see now why I treat Lucy the way I do and have so much respect for her? When I first met her I knew there was something special not knowing that she lost her penis and testicles in that accident. It was feeling something special about her that not having those body parts didn't matter to me. Seeing Lucy sit to pee like a woman didn't bother me at all. When Lucy learned that I liked cross dressing men and had some gay friends she didn't run where most guys would have been gone. Now look at us with me a new Mistress and Lucy a new sissymaid.

Thanks for listening
Judy


Thank you for your letter Judy. You have an amazing relationship with Lucy and illustrates very well that not all Mistress/sissymaid relationships need to be adversarial, taking her feelings into consideration and showing tenderness for her seems to be as productive as the crop. Still maintaining your rightful place while showing kindness obviously is working very well for you both. So in answer to your question, yes, most any man can be a good sissymaid especially if he has a great Mistress.

Helga

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